Giorgio Chiellini’s opener was wiped out by Palermo winger Aleksandar Trajkovski, as uninspired Italy were held by Macedonia.
This result not only means Italy are guaranteed second place behind Spain in the group, but is also potentially disastrous for their ranking in the World Cup play-off draw.
The Azzurri had won every game in the group save for the draw and defeat to Spain, but still needed to secure a play-off spot for the 2018 World Cup. Missing Andrea Belotti, Claudio Marchisio, Daniele De Rossi, Marco Verratti, Lorenzo Pellegrini and Stephan El Shaarawy, Giampiero Ventura dropped the 4-2-4 system in favour of 3-4-3 in the Stadio Olimpico Grande Torino with Bologna’s Simone Verdi and Roberto Gagliardini getting their first senior Italy starts. Macedonia, beaten 3-2 in stoppages in Skopje last year, had defender Kire Ristevski suspended.
Gigi Buffon became the first Italy goalkeeper to wear Azzurri blue, as they debuted the new kit following a restyle of the FIGC logo.
Lorenzo Insigne and Ciro Immobile combined passes repeatedly at pace for the Napoli man to force a save from the on-rushing goalkeeper.
Gigi Buffon smothered a Goran Pandev half-volley at the near post after a ‘sombrero’ flick over defenders and Marco Parolo’s cross found Insigne for a free header, which he aimed straight at the goalkeeper.
Insigne’s assist then released Davide Zappacosta, but the Chelsea man’s first touch was dismal and he sliced it off target.
The Azzurri finally found a breakthrough on the follow-up from a corner, as Insigne’s through ball released Immobile and he generously rolled it across for Chiellini to tap in from six yards.
It was almost 1-1 moments later, as Leonardo Bonucci gave away possession on the edge of the box with a terrible pass, but Chiellini rushed across to force a corner.
Andrea Barzagli had a knock in the first half, so made way for Daniele Rugani, even though his Juventus teammate dislocated a finger in training this week.
Federico Bernardeschi replaced debutant Verdi and Buffon took the sting out of a sudden Stefan Spirovski snapshot from distance.
The first real test for Buffon was a free header from Palermo striker Ilija Nestorovski that was well smothered on the ground.
It was a warning that Italy did not heed and Macedonia got an equaliser with two Peninsula-based players. Pandev of Genoa threaded through for Palermo winger Aleksandar Trajkovski, who burst into the box down the right relatively undisturbed and blasted the finish across Buffon into the far bottom corner.
Federico Bernardeschi fired wide from distance, but there was precious little reaction and the jeers began to rain down from the stands.
Italy 1-1 Macedonia
Chiellini 40 (I), Trajkovski 77 (M)
Italy: Buffon; Barzagli (Rugani 46), Bonucci, Chiellini; Zappacosta, Parolo, Gagliardini (Cristante 75), Darmian; Verdi (Bernardeschi 63), Immobile, Insigne
Macedonia: Dimitrievski; Ristovski, Musliu, Velkoski (Zajkov 75); Radeski, Spirovski, Bardi, Alioski; Pandev (Trickovski 80), Nestorovski, Hasani (Trajkovski 63)
Ref: Martins (POR)